NPASS Compound

Structure

CID51070 OpenBabel06191715382D 27 29 0 0 1 0 0 0 0 0999 V2000 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6962 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 20 1 0 0 0 0 3 5 1 0 0 0 0 3 10 2 0 0 0 0 4 6 2 0 0 0 0 4 10 1 0 0 0 0 5 11 2 0 0 0 0 6 11 1 0 0 0 0 7 12 1 0 0 0 0 7 16 1 0 0 0 0 8 14 2 0 0 0 0 8 15 1 0 0 0 0 9 13 2 0 0 0 0 9 27 1 0 0 0 0 10 13 1 0 0 0 0 11 21 1 0 0 0 0 12 14 1 0 0 0 0 12 18 2 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 20 1 0 0 0 0 16 23 1 6 0 0 0 17 18 1 0 0 0 0 17 19 1 0 0 0 0 18 24 1 0 0 0 0 19 25 2 0 0 0 0 20 26 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	372.12
Volume:	369.247
LogP:	2.021
LogD:	1.791
LogS:	-3.145
# Rotatable Bonds:	4
TPSA:	131.36
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.475
Synthetic Accessibility Score:	3.254
Fsp3:	0.25
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.052
MDCK Permeability:	7.2648326749913394e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.98
Human Intestinal Absorption (HIA):	0.017
20% Bioavailability (F20%):	0.663
30% Bioavailability (F30%):	0.894

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	96.7156753540039%
Volume Distribution (VD):	0.476
Pgp-substrate:	3.452423572540283%

ADMET: Metabolism

CYP1A2-inhibitor:	0.56
CYP1A2-substrate:	0.102
CYP2C19-inhibitor:	0.055
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.623
CYP2C9-substrate:	0.696
CYP2D6-inhibitor:	0.572
CYP2D6-substrate:	0.23
CYP3A4-inhibitor:	0.133
CYP3A4-substrate:	0.113

ADMET: Excretion

Clearance (CL):	7.396
Half-life (T1/2):	0.873

ADMET: Toxicity

hERG Blockers:	0.04
Human Hepatotoxicity (H-HT):	0.098
Drug-inuced Liver Injury (DILI):	0.412
AMES Toxicity:	0.114
Rat Oral Acute Toxicity:	0.828
Maximum Recommended Daily Dose:	0.725
Skin Sensitization:	0.89
Carcinogencity:	0.215
Eye Corrosion:	0.003
Eye Irritation:	0.233
Respiratory Toxicity:	0.081

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC51070

Natural Product ID:	NPC51070
*Common Name:**	Erycibenin A
IUPAC Name:	6-[(2S)-2,3-dihydroxy-3-methylbutyl]-5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
Synonyms:
Standard InCHIKey:	ZTEAOMCBLMDBDX-INIZCTEOSA-N
Standard InCHI:	InChI=1S/C20H20O7/c1-20(2,26)16(23)7-12-14(22)8-15-17(18(12)24)19(25)13(9-27-15)10-3-5-11(21)6-4-10/h3-6,8-9,16,21-24,26H,7H2,1-2H3/t16-/m0/s1
SMILES:	Oc1ccc(cc1)c1coc2c(c1=O)c(O)c(c(c2)O)C[C@@H](C(O)(C)C)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL241817
PubChem CID:	11337736
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0001612] Isoflavans [CHEMONTID:0001827] Isoflavanones [CHEMONTID:0003526] 6-prenylated isoflavanones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	stem	n.a.	PMID[17077549]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	stems	n.a.	n.a.	PMID[17158054]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26058	Erycibe expansa	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3

Activity Type	# Activity
Cell Line	3

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	46000.0	nM	PMID[536097]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	25000.0	nM	PMID[536097]
NPT466	Cell Line	U-937	Homo sapiens	IC50	=	21000.0	nM	PMID[536097]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC51070 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	395
0.1-0.2	1600
0.2-0.3	3720
0.3-0.4	9278
0.4-0.5	9376
0.5-0.6	3748
0.6-0.7	5530
0.7-0.8	4673
0.8-0.85	2181
0.85-0.9	1791
0.9-0.95	340
0.95-1	65

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC222298
0.9787	High Similarity	NPC316769
0.9786	High Similarity	NPC475705
0.9786	High Similarity	NPC476178
0.9786	High Similarity	NPC117836
0.9786	High Similarity	NPC51887
0.9643	High Similarity	NPC321980
0.9643	High Similarity	NPC469404
0.9643	High Similarity	NPC470087
0.9589	High Similarity	NPC7989
0.9589	High Similarity	NPC223701
0.9589	High Similarity	NPC472583
0.9586	High Similarity	NPC472422
0.9586	High Similarity	NPC471676
0.9586	High Similarity	NPC244577
0.9586	High Similarity	NPC472420
0.9586	High Similarity	NPC263384
0.9583	High Similarity	NPC89442
0.9571	High Similarity	NPC204985
0.9571	High Similarity	NPC215311
0.9571	High Similarity	NPC172250
0.9571	High Similarity	NPC259166
0.9571	High Similarity	NPC219917
0.9571	High Similarity	NPC213659
0.9571	High Similarity	NPC80962
0.9571	High Similarity	NPC48624
0.9571	High Similarity	NPC144118
0.9571	High Similarity	NPC326109
0.9524	High Similarity	NPC470681
0.9521	High Similarity	NPC323626
0.9521	High Similarity	NPC31627
0.9521	High Similarity	NPC324233
0.9521	High Similarity	NPC476238
0.9521	High Similarity	NPC285623
0.9521	High Similarity	NPC327269
0.9517	High Similarity	NPC177308
0.9517	High Similarity	NPC61258
0.9517	High Similarity	NPC124478
0.9507	High Similarity	NPC245482
0.9507	High Similarity	NPC301751
0.9504	High Similarity	NPC52789
0.9504	High Similarity	NPC470089
0.9504	High Similarity	NPC268204
0.9504	High Similarity	NPC55832
0.9504	High Similarity	NPC26051
0.95	High Similarity	NPC283429
0.95	High Similarity	NPC295384
0.95	High Similarity	NPC470211
0.9456	High Similarity	NPC469405
0.9452	High Similarity	NPC474772
0.9452	High Similarity	NPC472423
0.9452	High Similarity	NPC474744
0.9452	High Similarity	NPC471675
0.9452	High Similarity	NPC471677
0.9448	High Similarity	NPC5173
0.9444	High Similarity	NPC472627
0.9441	High Similarity	NPC224714
0.9437	High Similarity	NPC148545
0.9433	High Similarity	NPC253822
0.9433	High Similarity	NPC101366
0.9429	High Similarity	NPC21350
0.9392	High Similarity	NPC217706
0.9392	High Similarity	NPC207809
0.9392	High Similarity	NPC259710
0.9392	High Similarity	NPC48579
0.9392	High Similarity	NPC304207
0.9392	High Similarity	NPC477958
0.9388	High Similarity	NPC171651
0.9388	High Similarity	NPC473996
0.9388	High Similarity	NPC475790
0.9388	High Similarity	NPC244583
0.9388	High Similarity	NPC243171
0.9388	High Similarity	NPC150123
0.9388	High Similarity	NPC35567
0.9388	High Similarity	NPC56232
0.9388	High Similarity	NPC161881
0.9388	High Similarity	NPC10807
0.9384	High Similarity	NPC472421
0.9379	High Similarity	NPC168085
0.9379	High Similarity	NPC6511
0.9375	High Similarity	NPC472629
0.9371	High Similarity	NPC95751
0.9362	High Similarity	NPC201541
0.9357	High Similarity	NPC209560
0.9357	High Similarity	NPC294409
0.9357	High Similarity	NPC303644
0.9357	High Similarity	NPC162680
0.9357	High Similarity	NPC181124
0.9357	High Similarity	NPC317119
0.9357	High Similarity	NPC116632
0.9357	High Similarity	NPC7013
0.9324	High Similarity	NPC293286
0.9324	High Similarity	NPC180301
0.9324	High Similarity	NPC248793
0.932	High Similarity	NPC474021
0.932	High Similarity	NPC254412
0.932	High Similarity	NPC262039
0.932	High Similarity	NPC472580
0.932	High Similarity	NPC278476
0.932	High Similarity	NPC472636
0.932	High Similarity	NPC209846
0.932	High Similarity	NPC474023
0.932	High Similarity	NPC328740
0.932	High Similarity	NPC289774
0.932	High Similarity	NPC262038
0.932	High Similarity	NPC477897
0.932	High Similarity	NPC319910
0.9315	High Similarity	NPC317492
0.9315	High Similarity	NPC171916
0.9315	High Similarity	NPC38545
0.9315	High Similarity	NPC472628
0.931	High Similarity	NPC296998
0.931	High Similarity	NPC104406
0.931	High Similarity	NPC97716
0.931	High Similarity	NPC237635
0.931	High Similarity	NPC79469
0.931	High Similarity	NPC24673
0.931	High Similarity	NPC23728
0.931	High Similarity	NPC201731
0.931	High Similarity	NPC110303
0.931	High Similarity	NPC85773
0.931	High Similarity	NPC473077
0.9306	High Similarity	NPC476055
0.9306	High Similarity	NPC234629
0.9306	High Similarity	NPC311741
0.9306	High Similarity	NPC470890
0.9306	High Similarity	NPC87486
0.9306	High Similarity	NPC209040
0.9306	High Similarity	NPC124780
0.9301	High Similarity	NPC226636
0.9301	High Similarity	NPC11561
0.9291	High Similarity	NPC90665
0.9291	High Similarity	NPC55162
0.9291	High Similarity	NPC12175
0.9291	High Similarity	NPC278323
0.9291	High Similarity	NPC309154
0.9291	High Similarity	NPC279668
0.9286	High Similarity	NPC98115
0.9286	High Similarity	NPC249606
0.9286	High Similarity	NPC41461
0.9286	High Similarity	NPC25287
0.9286	High Similarity	NPC12165
0.9286	High Similarity	NPC477242
0.9286	High Similarity	NPC150399
0.9286	High Similarity	NPC1486
0.9286	High Similarity	NPC477244
0.9286	High Similarity	NPC274109
0.9286	High Similarity	NPC168105
0.9286	High Similarity	NPC66349
0.9286	High Similarity	NPC477243
0.9286	High Similarity	NPC186838
0.9262	High Similarity	NPC304745
0.9262	High Similarity	NPC111341
0.9262	High Similarity	NPC477530
0.9257	High Similarity	NPC477957
0.9257	High Similarity	NPC217149
0.9257	High Similarity	NPC256141
0.9257	High Similarity	NPC216035
0.9257	High Similarity	NPC138288
0.9252	High Similarity	NPC472633
0.9252	High Similarity	NPC105136
0.9252	High Similarity	NPC37348
0.9247	High Similarity	NPC160821
0.9247	High Similarity	NPC132592
0.9247	High Similarity	NPC166036
0.9247	High Similarity	NPC238279
0.9247	High Similarity	NPC266572
0.9247	High Similarity	NPC10097
0.9247	High Similarity	NPC203077
0.9241	High Similarity	NPC301276
0.9241	High Similarity	NPC267375
0.9241	High Similarity	NPC214774
0.9241	High Similarity	NPC474302
0.9241	High Similarity	NPC312973
0.9241	High Similarity	NPC20488
0.9241	High Similarity	NPC83357
0.9241	High Similarity	NPC176229
0.9241	High Similarity	NPC142405
0.9241	High Similarity	NPC246948
0.9241	High Similarity	NPC54577
0.9241	High Similarity	NPC67805
0.9241	High Similarity	NPC88964
0.9241	High Similarity	NPC470647
0.9241	High Similarity	NPC124729
0.9241	High Similarity	NPC475052
0.9241	High Similarity	NPC111786
0.9241	High Similarity	NPC195621
0.9236	High Similarity	NPC310130
0.9236	High Similarity	NPC149026
0.9236	High Similarity	NPC106985
0.9236	High Similarity	NPC75049
0.9236	High Similarity	NPC150408
0.9236	High Similarity	NPC68104
0.9236	High Similarity	NPC91560
0.9236	High Similarity	NPC478086
0.9236	High Similarity	NPC221432
0.9236	High Similarity	NPC166138
0.9236	High Similarity	NPC169591
0.9236	High Similarity	NPC175504
0.9236	High Similarity	NPC214166

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC51070 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	362
0.1-0.2	918
0.2-0.3	1639
0.3-0.4	2631
0.4-0.5	1923
0.5-0.6	1104
0.6-0.7	385
0.7-0.8	122
0.8-0.85	44
0.85-0.9	18
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9517	High Similarity	NPD4380	Phase 2
0.9214	High Similarity	NPD1510	Phase 2
0.9172	High Similarity	NPD4378	Clinical (unspecified phase)
0.9067	High Similarity	NPD2393	Clinical (unspecified phase)
0.8929	High Similarity	NPD1240	Approved
0.8912	High Similarity	NPD7410	Clinical (unspecified phase)
0.8889	High Similarity	NPD4381	Clinical (unspecified phase)
0.8889	High Similarity	NPD1549	Phase 2
0.8889	High Similarity	NPD7075	Discontinued
0.8881	High Similarity	NPD2796	Approved
0.8874	High Similarity	NPD6801	Discontinued
0.8819	High Similarity	NPD1552	Clinical (unspecified phase)
0.8819	High Similarity	NPD1550	Clinical (unspecified phase)
0.8816	High Similarity	NPD7096	Clinical (unspecified phase)
0.8803	High Similarity	NPD1607	Approved
0.875	High Similarity	NPD1934	Approved
0.8636	High Similarity	NPD8443	Clinical (unspecified phase)
0.8625	High Similarity	NPD7804	Clinical (unspecified phase)
0.8591	High Similarity	NPD1511	Approved
0.8571	High Similarity	NPD2801	Approved
0.8562	High Similarity	NPD7411	Suspended
0.8477	Intermediate Similarity	NPD1512	Approved
0.8467	Intermediate Similarity	NPD6799	Approved
0.8452	Intermediate Similarity	NPD7819	Suspended
0.8447	Intermediate Similarity	NPD3818	Discontinued
0.8438	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD6166	Phase 2
0.8438	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.8367	Intermediate Similarity	NPD2935	Discontinued
0.8344	Intermediate Similarity	NPD3882	Suspended
0.8301	Intermediate Similarity	NPD5403	Approved
0.8282	Intermediate Similarity	NPD7054	Approved
0.828	Intermediate Similarity	NPD3817	Phase 2
0.8267	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8258	Intermediate Similarity	NPD6599	Discontinued
0.825	Intermediate Similarity	NPD6959	Discontinued
0.8242	Intermediate Similarity	NPD6559	Discontinued
0.8232	Intermediate Similarity	NPD7472	Approved
0.8232	Intermediate Similarity	NPD7074	Phase 3
0.8228	Intermediate Similarity	NPD7768	Phase 2
0.821	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.82	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.8199	Intermediate Similarity	NPD6232	Discontinued
0.8187	Intermediate Similarity	NPD5494	Approved
0.8182	Intermediate Similarity	NPD6797	Phase 2
0.817	Intermediate Similarity	NPD5401	Approved
0.8165	Intermediate Similarity	NPD5402	Approved
0.8163	Intermediate Similarity	NPD6651	Approved
0.816	Intermediate Similarity	NPD7473	Discontinued
0.8146	Intermediate Similarity	NPD3750	Approved
0.8133	Intermediate Similarity	NPD7251	Discontinued
0.8133	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD7808	Phase 3
0.8079	Intermediate Similarity	NPD2800	Approved
0.8065	Intermediate Similarity	NPD920	Approved
0.8052	Intermediate Similarity	NPD2532	Approved
0.8052	Intermediate Similarity	NPD2534	Approved
0.8052	Intermediate Similarity	NPD2533	Approved
0.8027	Intermediate Similarity	NPD943	Approved
0.8026	Intermediate Similarity	NPD4628	Phase 3
0.8	Intermediate Similarity	NPD1551	Phase 2
0.7976	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7976	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7961	Intermediate Similarity	NPD1243	Approved
0.7952	Intermediate Similarity	NPD5844	Phase 1
0.795	Intermediate Similarity	NPD3749	Approved
0.7935	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7933	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7922	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD2313	Discontinued
0.7862	Intermediate Similarity	NPD2798	Approved
0.7857	Intermediate Similarity	NPD5953	Discontinued
0.7844	Intermediate Similarity	NPD7286	Phase 2
0.7816	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7815	Intermediate Similarity	NPD7033	Discontinued
0.7815	Intermediate Similarity	NPD3748	Approved
0.7815	Intermediate Similarity	NPD2799	Discontinued
0.7756	Intermediate Similarity	NPD7390	Discontinued
0.7751	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.774	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD4360	Phase 2
0.7727	Intermediate Similarity	NPD4363	Phase 3
0.7712	Intermediate Similarity	NPD2344	Approved
0.7703	Intermediate Similarity	NPD3027	Phase 3
0.7697	Intermediate Similarity	NPD1247	Approved
0.7683	Intermediate Similarity	NPD919	Approved
0.7651	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.765	Intermediate Similarity	NPD7584	Approved
0.7639	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD3226	Approved
0.7625	Intermediate Similarity	NPD7458	Discontinued
0.7616	Intermediate Similarity	NPD5124	Phase 1
0.7616	Intermediate Similarity	NPD230	Phase 1
0.7616	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.761	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7551	Intermediate Similarity	NPD1203	Approved
0.755	Intermediate Similarity	NPD1613	Approved
0.755	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7532	Intermediate Similarity	NPD6099	Approved
0.7532	Intermediate Similarity	NPD6100	Approved
0.7517	Intermediate Similarity	NPD6832	Phase 2
0.7517	Intermediate Similarity	NPD4908	Phase 1
0.7516	Intermediate Similarity	NPD2309	Approved
0.7514	Intermediate Similarity	NPD6782	Approved
0.7514	Intermediate Similarity	NPD6779	Approved
0.7514	Intermediate Similarity	NPD6778	Approved
0.7514	Intermediate Similarity	NPD6776	Approved
0.7514	Intermediate Similarity	NPD6780	Approved
0.7514	Intermediate Similarity	NPD6777	Approved
0.7514	Intermediate Similarity	NPD6781	Approved
0.75	Intermediate Similarity	NPD2654	Approved
0.7486	Intermediate Similarity	NPD4362	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD4361	Phase 2
0.7484	Intermediate Similarity	NPD2346	Discontinued
0.7483	Intermediate Similarity	NPD1548	Phase 1
0.7471	Intermediate Similarity	NPD3751	Discontinued
0.7468	Intermediate Similarity	NPD4308	Phase 3
0.7468	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD3972	Approved
0.7452	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.744	Intermediate Similarity	NPD5710	Approved
0.744	Intermediate Similarity	NPD5711	Approved
0.7439	Intermediate Similarity	NPD1465	Phase 2
0.7436	Intermediate Similarity	NPD2424	Discontinued
0.7423	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7417	Intermediate Similarity	NPD3268	Approved
0.7414	Intermediate Similarity	NPD8313	Approved
0.7414	Intermediate Similarity	NPD8312	Approved
0.7405	Intermediate Similarity	NPD6190	Approved
0.7401	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7397	Intermediate Similarity	NPD1610	Phase 2
0.7396	Intermediate Similarity	NPD3926	Phase 2
0.7391	Intermediate Similarity	NPD7435	Discontinued
0.7386	Intermediate Similarity	NPD8434	Phase 2
0.7386	Intermediate Similarity	NPD8150	Discontinued
0.7378	Intermediate Similarity	NPD37	Approved
0.7361	Intermediate Similarity	NPD9545	Approved
0.7347	Intermediate Similarity	NPD9717	Approved
0.7343	Intermediate Similarity	NPD9493	Approved
0.7342	Intermediate Similarity	NPD7003	Approved
0.7341	Intermediate Similarity	NPD3823	Discontinued
0.7337	Intermediate Similarity	NPD3787	Discontinued
0.7315	Intermediate Similarity	NPD1164	Approved
0.7315	Intermediate Similarity	NPD1470	Approved
0.7315	Intermediate Similarity	NPD2797	Approved
0.7308	Intermediate Similarity	NPD5405	Approved
0.7308	Intermediate Similarity	NPD5404	Approved
0.7308	Intermediate Similarity	NPD5406	Approved
0.7308	Intermediate Similarity	NPD5408	Approved
0.7303	Intermediate Similarity	NPD6798	Discontinued
0.7303	Intermediate Similarity	NPD3764	Approved
0.7301	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD7696	Phase 3
0.7297	Intermediate Similarity	NPD7697	Approved
0.7297	Intermediate Similarity	NPD7698	Approved
0.7287	Intermediate Similarity	NPD8151	Discontinued
0.7285	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7283	Intermediate Similarity	NPD1729	Discontinued
0.7279	Intermediate Similarity	NPD1201	Approved
0.7279	Intermediate Similarity	NPD422	Phase 1
0.7278	Intermediate Similarity	NPD1652	Phase 2
0.7273	Intermediate Similarity	NPD6844	Discontinued
0.7273	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD4661	Approved
0.7267	Intermediate Similarity	NPD4662	Approved
0.7267	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD6234	Discontinued
0.7258	Intermediate Similarity	NPD7870	Phase 2
0.7258	Intermediate Similarity	NPD7871	Phase 2
0.7246	Intermediate Similarity	NPD4967	Phase 2
0.7246	Intermediate Similarity	NPD4965	Approved
0.7246	Intermediate Similarity	NPD4966	Approved
0.7243	Intermediate Similarity	NPD6823	Phase 2
0.7238	Intermediate Similarity	NPD6535	Approved
0.7238	Intermediate Similarity	NPD6534	Approved
0.7237	Intermediate Similarity	NPD4625	Phase 3
0.7234	Intermediate Similarity	NPD7701	Phase 2
0.7234	Intermediate Similarity	NPD7585	Approved
0.7232	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7229	Intermediate Similarity	NPD5760	Phase 2
0.7229	Intermediate Similarity	NPD8455	Phase 2
0.7229	Intermediate Similarity	NPD5761	Phase 2
0.7228	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD9494	Approved
0.7208	Intermediate Similarity	NPD4307	Phase 2
0.7205	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD7685	Pre-registration
0.7186	Intermediate Similarity	NPD4288	Approved
0.7181	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD7583	Approved
0.7176	Intermediate Similarity	NPD7199	Phase 2
0.7161	Intermediate Similarity	NPD1933	Approved
0.7161	Intermediate Similarity	NPD447	Suspended
0.7161	Intermediate Similarity	NPD6355	Discontinued
0.716	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7158	Intermediate Similarity	NPD7874	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data